Octocrylene is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...

used as an ingredient in

sunscreen Sunscreen, also known as sunblock or sun cream, is a photoprotective topical product for the skin that mainly absorbs, or to a much lesser extent reflects, some of the sun's ultraviolet (UV) radiation and thus helps protect against sunbur ...

s and cosmetics. It is an

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ...

formed by the condensation of 2-ethylhexyl cyanoacetate with

benzophenone Benzophenone is the organic compound with the formula (C6H5)2CO, generally abbreviated Ph2CO. It is a white solid that is soluble in organic solvents. Benzophenone is a widely used building block in organic chemistry, being the parent diarylket ...

. It is a viscous, oily liquid that is clear and colorless. The extended

conjugation Conjugation or conjugate may refer to: Linguistics *Grammatical conjugation, the modification of a verb from its basic form * Emotive conjugation or Russell's conjugation, the use of loaded language Mathematics *Complex conjugation, the change ...

of the

acrylate Acrylates (IUPAC: prop-2-enoates) are the salts, esters, and conjugate bases of acrylic acid. The acrylate ion is the anion C H2=CHC OO−. Often, acrylate refers to esters of acrylic acid, the most common member being methyl acrylate. These acr ...

portion of the molecule absorbs UVB and short-wave UVA (

ultraviolet Ultraviolet (UV) is a form of electromagnetic radiation with wavelength from 10 nm (with a corresponding frequency around 30 PHz) to 400 nm (750 THz), shorter than that of visible light, but longer than X-rays. UV radiation ...

) rays with wavelengths from 280 to 320 nm, protecting the skin from

direct DNA damage Direct may refer to: Mathematics * Directed set, in order theory * Direct limit of (pre), sheaves * Direct sum of modules, a construction in abstract algebra which combines several vector spaces Computing * Direct access (disambiguation), ...

. The ethylhexanol portion is a

fatty alcohol Fatty alcohols (or long-chain alcohols) are usually high-molecular-weight, straight-chain primary alcohols, but can also range from as few as 4–6 carbons to as many as 22–26, derived from natural fats and oils. The precise chain length varies ...

, adding

emollient A moisturizer, or emollient, is a cosmetic preparation used for protecting, moisturizing, and lubricating the skin. These functions are normally performed by sebum produced by healthy skin. The word "emollient" is derived from the Latin verb ''m ...

and oil-like (water resistant) properties.

Safety

Octocrylene can penetrate into the skin where it acts as a

photosensitizer Photosensitizers produce a physicochemical change in a neighboring molecule by either donating an electron to the substrate or by abstracting a hydrogen atom from the substrate. At the end of this process, the photosensitizer eventually returns t ...

, resulting in an increased production of free radicals under illumination. It may also pass through the skin, into the blood stream, eventually being metabolized and excreted in urine in form of its metabolites. Octocrylene can convert to

through a retro- aldol condensation. The reaction occurs slowly over time, yielding significant concentration of benzophenone in all commercial cosmetics tested formulated with octocrylene. In coral, octocrylene has been shown to accumulate in the form of fatty acid conjugates and trigger mitochondrial dysfunction.

Regulation

Palau Palau,, officially the Republic of Palau and historically ''Belau'', ''Palaos'' or ''Pelew'', is an island country and microstate in the western Pacific. The nation has approximately 340 islands and connects the western chain of the ...

banned the sale and use of 3 reef toxic UV filters including octocrylene in its Responsible Tourism Education Act of 2018.

References

{{Sunscreening agents Carboxylate esters Household chemicals Sunscreening agents

Safety

Regulation

See also

References